title: Flexible strategy for syntheses of spirooxindoles using palladium-catalyzed carbosilylation and Sakurai-type cyclization.
abstract: The intramolecular carbosilylation of N-[2-(1,3-butenyl)aryl]carbamoyl chloride has been investigated. The reaction with hexamethyldisilane proceeds smoothly in the presence of a catalytic amount of [Pd(η(3)-allyl)Cl](2) to give oxindoles with an allylsilane functional group in good yield. The subsequent subjection of the products to a Sakurai-type reaction provides more advanced tricyclic spirooxindoles by controlling the stereochemistry of three contiguous stereogenic centers.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Sudhir M
authors.initials: SM
authors.lastname: Hande
authors.forename: Motoyuki
authors.initials: M
authors.lastname: Nakajima
authors.forename: Haruhi
authors.initials: H
authors.lastname: Kamisaki
authors.forename: Chihiro
authors.initials: C
authors.lastname: Tsukano
authors.forename: Yoshiji
authors.initials: Y
authors.lastname: Takemoto
mesh_terms: D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D000078183:Oxindoles; D010165:Palladium / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis*
chemical_list: D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole; D010165:Palladium